NPASS Compound

Structure

NPC240130 OpenBabel07101719182D 71 74 0 0 1 0 0 0 0 0999 V2000 -2.0221 3.3187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6570 1.2021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1967 1.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4856 -0.0205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4422 -1.9795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9338 3.6601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8726 1.7786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9529 -7.4053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7959 -6.9186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1098 -6.9186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5102 -4.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6852 3.0412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7959 -5.9451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1098 -5.9451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6187 -4.8474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6323 -2.7815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5546 -1.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4473 -3.3139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3696 -1.9023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5742 -4.6286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1481 -3.9953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6173 -3.4887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0560 -0.7445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9529 -4.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8677 -0.1170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9811 1.3876 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7341 -0.6394 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9529 -5.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6859 -1.8094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3159 -2.8743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8342 -4.2708 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7116 -5.4722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1162 0.5018 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1873 -1.1841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1098 -3.9980 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5250 2.0810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0011 -4.0491 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7794 0.2243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8740 0.4200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2209 -1.4824 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1364 -4.9496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2045 0.1605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6108 -0.3996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4075 -2.4379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6615 -5.2593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4511 -3.0863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9020 0.3663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6159 -2.1300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8315 -1.5535 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5074 -1.7390 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5088 -3.0976 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2765 1.4621 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2738 -3.4022 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7440 -5.3651 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8108 0.1551 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0443 -0.7997 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4779 -2.1132 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4909 -4.7495 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.1309 -3.4068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6133 1.7396 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4779 -3.2003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5309 -0.3946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9397 1.1845 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6912 -5.7497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4531 0.7794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2896 0.2982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3807 -2.4111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0279 -6.1613 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4066 -3.2730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6891 1.3163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 5 57 1 0 0 0 0 6 12 1 0 0 0 0 7 26 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 36 1 0 0 0 0 13 28 2 0 0 0 0 14 28 1 0 0 0 0 16 18 1 0 0 0 0 16 29 2 0 0 0 0 17 19 2 0 0 0 0 17 29 1 0 0 0 0 18 30 2 0 0 0 0 19 30 1 0 0 0 0 20 21 1 0 0 0 0 21 37 1 0 0 0 0 22 51 1 0 0 0 0 23 29 1 0 0 0 0 24 28 1 0 0 0 0 25 38 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 27 40 1 0 0 0 0 27 71 1 0 0 0 0 30 59 1 0 0 0 0 31 15 1 6 0 0 0 31 41 1 0 0 0 0 31 53 1 0 0 0 0 32 20 1 6 0 0 0 32 45 1 0 0 0 0 32 54 1 0 0 0 0 33 25 1 6 0 0 0 33 42 1 0 0 0 0 33 52 1 0 0 0 0 34 23 1 6 0 0 0 34 43 1 0 0 0 0 34 57 1 0 0 0 0 35 24 1 6 0 0 0 35 46 1 0 0 0 0 35 58 1 0 0 0 0 36 52 2 3 0 0 0 36 60 1 0 0 0 0 37 58 1 0 0 0 0 37 61 1 1 0 0 0 38 62 2 0 0 0 0 38 63 1 0 0 0 0 39 26 1 6 0 0 0 39 47 1 0 0 0 0 39 55 1 0 0 0 0 40 44 1 0 0 0 0 40 56 1 1 0 0 0 41 54 2 3 0 0 0 41 64 1 0 0 0 0 42 56 2 3 0 0 0 42 65 1 0 0 0 0 43 55 2 3 0 0 0 43 66 1 0 0 0 0 44 53 2 3 0 0 0 44 67 1 0 0 0 0 45 58 1 0 0 0 0 45 68 2 0 0 0 0 46 57 1 0 0 0 0 46 69 2 0 0 0 0 47 70 2 0 0 0 0 47 71 1 0 0 0 0 48 49 2 0 0 0 0 48 50 1 0 0 0 0 48 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	992.5
Volume:	986.595
LogP:	0.236
LogD:	0.011
LogS:	-1.92
# Rotatable Bonds:	20
TPSA:	355.57
# H-Bond Aceptor:	23
# H-Bond Donor:	12
# Rings:	4
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.043
Synthetic Accessibility Score:	6.931
Fsp3:	0.542
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-7.445
MDCK Permeability:	5.345845056581311e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.967
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	49.64282989501953%
Volume Distribution (VD):	0.376
Pgp-substrate:	44.2459716796875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.027
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.214
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	2.369
Half-life (T1/2):	0.845

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.826
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.514
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.376
Carcinogencity:	0.206
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.772

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC240130

Natural Product ID:	NPC240130
*Common Name:**	Micropeptin Ei992
IUPAC Name:	(3S)-4-[[(2S,5S,8S,11R,12S,15S,18S,21R)-2-benzyl-8-[(2S)-butan-2-yl]-15-[3-(diaminomethylideneamino)propyl]-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-3-(butanoylamino)-4-oxobutanoic acid
Synonyms:	Micropeptin EI992
Standard InCHIKey:	YISRXUQQIVQAHS-QYVAUQPQSA-N
Standard InCHI:	InChI=1S/C48H68N10O13/c1-6-12-36(60)52-33(25-38(62)63)42(65)56-40-27(4)71-47(70)39(26(3)7-2)55-43(66)34(23-29-16-18-30(59)19-17-29)57(5)46(69)35(24-28-13-9-8-10-14-28)58-37(61)21-20-32(45(58)68)54-41(64)31(53-44(40)67)15-11-22-51-48(49)50/h8-10,13-14,16-19,26-27,31-35,37,39-40,59,61H,6-7,11-12,15,20-25H2,1-5H3,(H,52,60)(H,53,67)(H,54,64)(H,55,66)(H,56,65)(H,62,63)(H4,49,50,51)/t26-,27+,31-,32-,33-,34-,35-,37+,39-,40-/m0/s1
SMILES:	CCCC(=N[C@@H](CC(=O)O)C(=N[C@H]1[C@@H](C)OC(=O)[C@H]([C@@H](C)CC)N=C([C@H](Cc2ccc(cc2)O)N(C)C(=O)[C@H](Cc2ccccc2)N2[C@@H](CC[C@@H](C2=O)N=C([C@H](CCCNC(=N)N)N=C1O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255290
PubChem CID:	10996701
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11000050]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11374973]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Einan Reservoir in Israel	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18163584]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18558743]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18973386]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	water bloom of the cyanobacterium Microcystis aeruginosa	n.a.	n.a.	PMID[19650639]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	bloom material	Lake Kinneret, Israel	n.a.	PMID[22280481]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Kibbutz Geva, Israel	n.a.	PMID[23153007]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Water Reservoir near Kibbutz Hafetz Haim, Israel	n.a.	PMID[23718637]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[24261937]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24642434]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24868986]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29405714]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[29847132]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9249979]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9842728]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	Database[Title]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	3830.0	nM	PMID[485792]
NPT2	Others	Unspecified		IC50	=	3.8	ug.mL-1	PMID[485793]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC240130 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	1079
0.2-0.3	5043
0.3-0.4	12427
0.4-0.5	16114
0.5-0.6	6788
0.6-0.7	685
0.7-0.8	225
0.8-0.85	80
0.85-0.9	32
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC61332
0.9371	High Similarity	NPC302715
0.9353	High Similarity	NPC473404
0.9112	High Similarity	NPC306804
0.9107	High Similarity	NPC40234
0.9034	High Similarity	NPC102959
0.9006	High Similarity	NPC50016
0.8983	High Similarity	NPC60516
0.8902	High Similarity	NPC269750
0.8902	High Similarity	NPC194671
0.8889	High Similarity	NPC137627
0.8882	High Similarity	NPC198254
0.8882	High Similarity	NPC274198
0.8882	High Similarity	NPC46009
0.8852	High Similarity	NPC477551
0.8846	High Similarity	NPC477550
0.8846	High Similarity	NPC477552
0.8837	High Similarity	NPC279871
0.8837	High Similarity	NPC476227
0.8786	High Similarity	NPC196243
0.8779	High Similarity	NPC273755
0.8772	High Similarity	NPC276506
0.8772	High Similarity	NPC475123
0.8772	High Similarity	NPC475204
0.8765	High Similarity	NPC294516
0.8765	High Similarity	NPC107938
0.8728	High Similarity	NPC155506
0.8728	High Similarity	NPC159767
0.8721	High Similarity	NPC230611
0.8686	High Similarity	NPC45037
0.8659	High Similarity	NPC94862
0.8621	High Similarity	NPC473402
0.8548	High Similarity	NPC469443
0.8514	High Similarity	NPC473354
0.8492	Intermediate Similarity	NPC294951
0.8478	Intermediate Similarity	NPC477632
0.8478	Intermediate Similarity	NPC477638
0.8471	Intermediate Similarity	NPC469243
0.8457	Intermediate Similarity	NPC475532
0.843	Intermediate Similarity	NPC223207
0.8427	Intermediate Similarity	NPC153554
0.8409	Intermediate Similarity	NPC165285
0.8409	Intermediate Similarity	NPC471165
0.8409	Intermediate Similarity	NPC17698
0.8409	Intermediate Similarity	NPC26108
0.8391	Intermediate Similarity	NPC280022
0.8382	Intermediate Similarity	NPC471771
0.8382	Intermediate Similarity	NPC304074
0.8382	Intermediate Similarity	NPC290755
0.8371	Intermediate Similarity	NPC97526
0.8371	Intermediate Similarity	NPC119652
0.8363	Intermediate Similarity	NPC475544
0.8352	Intermediate Similarity	NPC248670
0.8304	Intermediate Similarity	NPC1390
0.8304	Intermediate Similarity	NPC62104
0.8287	Intermediate Similarity	NPC471049
0.8287	Intermediate Similarity	NPC471050
0.8287	Intermediate Similarity	NPC471048
0.8286	Intermediate Similarity	NPC129486
0.8281	Intermediate Similarity	NPC220060
0.8278	Intermediate Similarity	NPC476321
0.8276	Intermediate Similarity	NPC61004
0.8261	Intermediate Similarity	NPC473305
0.8261	Intermediate Similarity	NPC163961
0.8238	Intermediate Similarity	NPC469444
0.8235	Intermediate Similarity	NPC477639
0.8235	Intermediate Similarity	NPC473580
0.8232	Intermediate Similarity	NPC471526
0.8218	Intermediate Similarity	NPC63931
0.8172	Intermediate Similarity	NPC477631
0.8162	Intermediate Similarity	NPC477636
0.8158	Intermediate Similarity	NPC473450
0.8114	Intermediate Similarity	NPC22883
0.8114	Intermediate Similarity	NPC217804
0.8114	Intermediate Similarity	NPC210377
0.8114	Intermediate Similarity	NPC5719
0.8112	Intermediate Similarity	NPC469445
0.8101	Intermediate Similarity	NPC158277
0.8093	Intermediate Similarity	NPC219350
0.8093	Intermediate Similarity	NPC194699
0.809	Intermediate Similarity	NPC89831
0.8051	Intermediate Similarity	NPC478005
0.8042	Intermediate Similarity	NPC329295
0.8032	Intermediate Similarity	NPC65714
0.8023	Intermediate Similarity	NPC328649
0.8023	Intermediate Similarity	NPC63040
0.8022	Intermediate Similarity	NPC475564
0.8022	Intermediate Similarity	NPC475409
0.8022	Intermediate Similarity	NPC170302
0.8012	Intermediate Similarity	NPC473341
0.7966	Intermediate Similarity	NPC15068
0.7947	Intermediate Similarity	NPC473371
0.7937	Intermediate Similarity	NPC328763
0.7929	Intermediate Similarity	NPC469442
0.7929	Intermediate Similarity	NPC277306
0.7926	Intermediate Similarity	NPC473378
0.7926	Intermediate Similarity	NPC473407
0.7926	Intermediate Similarity	NPC248822
0.7912	Intermediate Similarity	NPC473546
0.7906	Intermediate Similarity	NPC471592
0.7882	Intermediate Similarity	NPC478007
0.788	Intermediate Similarity	NPC477637
0.785	Intermediate Similarity	NPC25539
0.7849	Intermediate Similarity	NPC299806
0.7849	Intermediate Similarity	NPC300443
0.7841	Intermediate Similarity	NPC114806
0.7805	Intermediate Similarity	NPC478008
0.7797	Intermediate Similarity	NPC241794
0.7784	Intermediate Similarity	NPC244336
0.7784	Intermediate Similarity	NPC24617
0.7772	Intermediate Similarity	NPC323662
0.7749	Intermediate Similarity	NPC314083
0.7746	Intermediate Similarity	NPC233702
0.774	Intermediate Similarity	NPC471527
0.7722	Intermediate Similarity	NPC302597
0.7719	Intermediate Similarity	NPC16188
0.7701	Intermediate Similarity	NPC202198
0.7701	Intermediate Similarity	NPC262166
0.7701	Intermediate Similarity	NPC56685
0.7688	Intermediate Similarity	NPC473491
0.768	Intermediate Similarity	NPC66490
0.7679	Intermediate Similarity	NPC214988
0.7679	Intermediate Similarity	NPC163392
0.7679	Intermediate Similarity	NPC48202
0.7679	Intermediate Similarity	NPC239762
0.7661	Intermediate Similarity	NPC81026
0.7657	Intermediate Similarity	NPC39431
0.7624	Intermediate Similarity	NPC209463
0.7614	Intermediate Similarity	NPC244509
0.7609	Intermediate Similarity	NPC136797
0.7602	Intermediate Similarity	NPC266741
0.7596	Intermediate Similarity	NPC328494
0.7588	Intermediate Similarity	NPC91953
0.7581	Intermediate Similarity	NPC475421
0.7579	Intermediate Similarity	NPC96275
0.7556	Intermediate Similarity	NPC471051
0.7556	Intermediate Similarity	NPC471053
0.7556	Intermediate Similarity	NPC471052
0.7529	Intermediate Similarity	NPC197921
0.7528	Intermediate Similarity	NPC323336
0.7528	Intermediate Similarity	NPC326349
0.7527	Intermediate Similarity	NPC141957
0.7514	Intermediate Similarity	NPC476268
0.7514	Intermediate Similarity	NPC472923
0.75	Intermediate Similarity	NPC51047
0.75	Intermediate Similarity	NPC122590
0.7485	Intermediate Similarity	NPC469360
0.7485	Intermediate Similarity	NPC168861
0.7474	Intermediate Similarity	NPC315542
0.746	Intermediate Similarity	NPC470903
0.746	Intermediate Similarity	NPC470112
0.746	Intermediate Similarity	NPC167763
0.7446	Intermediate Similarity	NPC473693
0.7446	Intermediate Similarity	NPC196091
0.7446	Intermediate Similarity	NPC471568
0.744	Intermediate Similarity	NPC267237
0.7432	Intermediate Similarity	NPC473502
0.743	Intermediate Similarity	NPC324850
0.7427	Intermediate Similarity	NPC476989
0.7414	Intermediate Similarity	NPC311658
0.7412	Intermediate Similarity	NPC132636
0.7409	Intermediate Similarity	NPC64140
0.7409	Intermediate Similarity	NPC174122
0.7402	Intermediate Similarity	NPC326333
0.7401	Intermediate Similarity	NPC5194
0.7401	Intermediate Similarity	NPC261934
0.7391	Intermediate Similarity	NPC186617
0.7389	Intermediate Similarity	NPC287757
0.7389	Intermediate Similarity	NPC319320
0.7382	Intermediate Similarity	NPC138083
0.7377	Intermediate Similarity	NPC254700
0.7358	Intermediate Similarity	NPC246591
0.7358	Intermediate Similarity	NPC234069
0.7356	Intermediate Similarity	NPC314114
0.7337	Intermediate Similarity	NPC242728
0.7333	Intermediate Similarity	NPC197743
0.7333	Intermediate Similarity	NPC297145
0.733	Intermediate Similarity	NPC326027
0.733	Intermediate Similarity	NPC2501
0.7326	Intermediate Similarity	NPC477462
0.7321	Intermediate Similarity	NPC326966
0.7321	Intermediate Similarity	NPC257390
0.7299	Intermediate Similarity	NPC209509
0.7292	Intermediate Similarity	NPC235194
0.7288	Intermediate Similarity	NPC7817
0.7288	Intermediate Similarity	NPC475168
0.7282	Intermediate Similarity	NPC470728
0.7259	Intermediate Similarity	NPC80514
0.7254	Intermediate Similarity	NPC276120
0.7236	Intermediate Similarity	NPC50548
0.7202	Intermediate Similarity	NPC325651
0.7194	Intermediate Similarity	NPC477526
0.7191	Intermediate Similarity	NPC324081
0.7186	Intermediate Similarity	NPC144314
0.7184	Intermediate Similarity	NPC161069
0.7173	Intermediate Similarity	NPC32064
0.7167	Intermediate Similarity	NPC470902
0.7151	Intermediate Similarity	NPC127741
0.7151	Intermediate Similarity	NPC6570
0.7143	Intermediate Similarity	NPC476978

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC240130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	388
0.2-0.3	706
0.3-0.4	1878
0.4-0.5	3270
0.5-0.6	2381
0.6-0.7	363
0.7-0.8	24
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8412	Intermediate Similarity	NPD8019	Approved
0.8382	Intermediate Similarity	NPD8303	Discontinued
0.8333	Intermediate Similarity	NPD7523	Phase 3
0.8198	Intermediate Similarity	NPD7495	Discontinued
0.7931	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD8076	Discontinued
0.7619	Intermediate Similarity	NPD6901	Phase 3
0.7566	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD8162	Phase 2
0.7525	Intermediate Similarity	NPD8163	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7978	Discontinued
0.7446	Intermediate Similarity	NPD7608	Discontinued
0.7409	Intermediate Similarity	NPD7617	Discontinued
0.7391	Intermediate Similarity	NPD7484	Phase 3
0.7391	Intermediate Similarity	NPD7485	Phase 3
0.7292	Intermediate Similarity	NPD6851	Approved
0.7292	Intermediate Similarity	NPD6853	Approved
0.7262	Intermediate Similarity	NPD3136	Phase 2
0.7247	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8031	Discontinued
0.7225	Intermediate Similarity	NPD7450	Phase 2
0.7207	Intermediate Similarity	NPD7131	Phase 3
0.72	Intermediate Similarity	NPD7811	Phase 3
0.72	Intermediate Similarity	NPD7810	Phase 3
0.7159	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6681	Discovery
0.7128	Intermediate Similarity	NPD6089	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5137	Approved
0.7119	Intermediate Similarity	NPD8323	Discontinued
0.7086	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6297	Approved
0.7076	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD4652	Approved
0.7056	Intermediate Similarity	NPD7613	Discontinued
0.7056	Intermediate Similarity	NPD7303	Discontinued
0.7052	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8292	Phase 2
0.6914	Remote Similarity	NPD6852	Discontinued
0.691	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD2098	Approved
0.6857	Remote Similarity	NPD8173	Phase 2
0.6857	Remote Similarity	NPD8172	Phase 2
0.6857	Remote Similarity	NPD6073	Approved
0.6854	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6796	Discontinued
0.6851	Remote Similarity	NPD6088	Approved
0.6845	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6294	Approved
0.6818	Remote Similarity	NPD6295	Approved
0.6816	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5967	Approved
0.6755	Remote Similarity	NPD2097	Approved
0.6754	Remote Similarity	NPD2889	Approved
0.6754	Remote Similarity	NPD2888	Approved
0.6754	Remote Similarity	NPD2017	Approved
0.6754	Remote Similarity	NPD2890	Approved
0.6751	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8025	Phase 2
0.6744	Remote Similarity	NPD4175	Approved
0.6744	Remote Similarity	NPD4177	Approved
0.6743	Remote Similarity	NPD5296	Approved
0.6743	Remote Similarity	NPD4153	Approved
0.6743	Remote Similarity	NPD6346	Approved
0.6724	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6419	Discontinued
0.672	Remote Similarity	NPD8417	Discontinued
0.6706	Remote Similarity	NPD4677	Discontinued
0.6686	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3400	Discontinued
0.6684	Remote Similarity	NPD5218	Approved
0.6684	Remote Similarity	NPD5219	Approved
0.6684	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7282	Approved
0.6667	Remote Similarity	NPD8356	Approved
0.6667	Remote Similarity	NPD5725	Approved
0.6667	Remote Similarity	NPD2568	Approved
0.665	Remote Similarity	NPD6967	Phase 2
0.6649	Remote Similarity	NPD5356	Approved
0.6649	Remote Similarity	NPD5355	Approved
0.6648	Remote Similarity	NPD6623	Phase 3
0.6648	Remote Similarity	NPD8416	Discontinued
0.6647	Remote Similarity	NPD2562	Approved
0.6647	Remote Similarity	NPD2561	Approved
0.6635	Remote Similarity	NPD6256	Approved
0.6635	Remote Similarity	NPD6255	Approved
0.6635	Remote Similarity	NPD6254	Approved
0.6629	Remote Similarity	NPD1330	Phase 2
0.6629	Remote Similarity	NPD3552	Approved
0.6629	Remote Similarity	NPD3554	Approved
0.6629	Remote Similarity	NPD3555	Approved
0.6629	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3553	Approved
0.6622	Remote Similarity	NPD8430	Approved
0.6613	Remote Similarity	NPD8315	Phase 1
0.661	Remote Similarity	NPD8643	Discontinued
0.6608	Remote Similarity	NPD4659	Approved
0.6607	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6863	Phase 2
0.6599	Remote Similarity	NPD5557	Phase 1
0.6599	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5747	Discontinued
0.659	Remote Similarity	NPD7451	Discontinued
0.6587	Remote Similarity	NPD6253	Approved
0.6582	Remote Similarity	NPD3909	Discontinued
0.6575	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3125	Approved
0.6566	Remote Similarity	NPD5445	Approved
0.6564	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2239	Approved
0.6556	Remote Similarity	NPD2240	Approved
0.6548	Remote Similarity	NPD42	Phase 2
0.6548	Remote Similarity	NPD6042	Phase 2
0.6545	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3536	Discontinued
0.6534	Remote Similarity	NPD5581	Approved
0.6532	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD4103	Phase 2
0.6526	Remote Similarity	NPD7972	Discontinued
0.6522	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.652	Remote Similarity	NPD5042	Phase 1
0.652	Remote Similarity	NPD7283	Approved
0.6517	Remote Similarity	NPD555	Phase 2
0.6514	Remote Similarity	NPD5263	Approved
0.6509	Remote Similarity	NPD8161	Suspended
0.6508	Remote Similarity	NPD6677	Suspended
0.6505	Remote Similarity	NPD6689	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6405	Approved
0.6497	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6407	Approved
0.6497	Remote Similarity	NPD5745	Approved
0.6492	Remote Similarity	NPD6646	Discontinued
0.6489	Remote Similarity	NPD3455	Phase 2
0.6481	Remote Similarity	NPD3879	Approved
0.648	Remote Similarity	NPD5314	Approved
0.648	Remote Similarity	NPD3054	Approved
0.648	Remote Similarity	NPD3052	Approved
0.6477	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD4086	Phase 1
0.6471	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD7281	Phase 3
0.6468	Remote Similarity	NPD7280	Phase 3
0.6459	Remote Similarity	NPD7565	Approved
0.6457	Remote Similarity	NPD3040	Approved
0.6455	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD3071	Approved
0.6453	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD3073	Approved
0.6453	Remote Similarity	NPD2584	Suspended
0.6453	Remote Similarity	NPD3072	Approved
0.6453	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD8271	Discontinued
0.6436	Remote Similarity	NPD6557	Phase 2
0.6435	Remote Similarity	NPD3878	Approved
0.6432	Remote Similarity	NPD7554	Discontinued
0.6432	Remote Similarity	NPD5485	Approved
0.6432	Remote Similarity	NPD5484	Approved
0.6432	Remote Similarity	NPD3519	Discontinued
0.6432	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5190	Phase 2
0.6429	Remote Similarity	NPD9568	Approved
0.6425	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7669	Phase 3
0.6425	Remote Similarity	NPD3908	Approved
0.6422	Remote Similarity	NPD4157	Discontinued
0.6417	Remote Similarity	NPD6390	Discontinued
0.6413	Remote Similarity	NPD6676	Phase 2
0.6411	Remote Similarity	NPD5856	Discontinued
0.641	Remote Similarity	NPD6107	Approved
0.6406	Remote Similarity	NPD7827	Phase 1
0.6404	Remote Similarity	NPD259	Phase 1
0.64	Remote Similarity	NPD4151	Approved
0.6395	Remote Similarity	NPD4761	Approved
0.6395	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4762	Approved
0.6394	Remote Similarity	NPD3964	Approved
0.6394	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4227	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data